ε-viniferin

Dimer

Identity

  • Sub structure Resveratrol dimers
  • Label : ε-viniferin
  • Synonyms :
    E-ε-Viniferin
    trans-ε-Viniferin
    (-)-ε-viniferin
  • Formula : C28H22O6
  • Molecular weight : 454.47
  • CAS Number : 62218-08-0
  • Comments MIB number: MIB-0312
  • References Amico, V., Barresi, V., Chillemi, R., Condorelli, D., Sciuto, S., Spatafora, C., Tringali, C., 2009. Bioassay-guided isolation of antiproliferative compounds from grape (Vitis vinifera) stems. Nat. Prod. Commun. 4, 27-34.
    Amira-Guebailia, H., Valls, J., Richard, T., Vitrac, X., Monti, J.-P., Delaunay, J.-C., Mérillon, J.-M., 2009. Centrifugal partition chromatography followed by HPLC for the isolation of cis-ε-viniferin, a resveratrol dimer newly extracted from a red Algerian wine. Food Chem. 113, 320-324.
    Barjot, C., Tournaire, M., Castagnino, C., Vigor, C., Vercauteren, J., Rossi, J.-F., 2007. Evaluation of Antitumor Effects of Two Vine Stalk Oligomers of Resveratrol on a Panel of Lymphoid and Myeloid Cell Lines: Comparison with Resveratrol. Life Sci. 81, 1565-1574.
    Bisson, J., Poupard, P., Pawlus, A. D., Pons, A., Darriet, P., Mérillon, J.-M., Waffo-Téguo, P., 2011. Development of hybrid elution systems for efficient purification of stilbenoids using centrifugal partition chromatography coupled to mass spectrometry J. Chromatogr. A 1218, 6079-6084.
    Chiou, W., Shen, C., Chen, C., Lin, C., Huang, Y., 2009. Oligostilbenes from the Roots of Vitis thunbergii. Planta Med. 75, 856-859.
    Guebailia, H.A., Chira, K., Richard, T., Mabrouk, T., Furiga, A., Vitrac, X., Monti, J.P., Delaunay, J.C., Mérillon, J.M., 2006. Hopeaphenol: The first resveratrol tetramer in wines from North Africa. J. Agric. Food. Chem. 54, 9559-9564.
    Ha, D. T., Kim, H., Thuong, P. T., Ngoc, T. M., Lee, I., Hung, N. D., Bae, K., 2009. Antioxidant and lipoxygenase inhibitory activity of oligostilbenes from the leaf and stem of Vitis amurensis. J. Ethnopharmacol. 125, 304-309.
    He, S., Jiang, L., Wu, B., Li, C., Pan, Y., 2009. Chunganenol: An Unusual Antioxidative Resveratrol Hexamer from Vitis chunganensis. J. Org. Chem. 74, 7966-7969.
    Huang, Y.-L., Tsai, W.-J., Shen, C.-C., Chen, C.-C., 2005. Resveratrol derivatives from the roots of Vitis thunbergii. J. Nat. Prod. 68, 217-220.
    Jean-Denis, J. B., Pezet, R., Tabacchi, R., 2006. Rapid analysis of stilbenes and derivatives from downy mildew-infected grapevine leaves by liquid chromatography-atmospheric pressure photoionisation mass spectrometry. J. Chromatogr. A 1112, 263-268.
    Kulesh, N. I., Veselova, M. V., Fedoreev, S. A., Denisenko, V. A., 2006. Polyphenols from Vitis amurensis Stems. Chem. Nat. Compd. 42, 235-237.
    Landrault, N., Larronde, F., Delaunay, J.-C., Castagnino, C., Vercauteren, J., Merillon, J.-M., Gasc, F., Cros, G., Teissedre, P.-L., 2002. Levels of stilbene oligomers and astilbin in French varietal wines and in grapes during noble rot development. Journal of Agricultral and Food Chemistry 50, 2046-2052.
    Langcake, P., 1981. Disease resistance of Vitis spp. and the production of the stress metabolites resveratrol, ε-viniferin, α-viniferin and pterostilbene. Physiol. Plant Pathol. 18, 213-226.
    Langcake, P., Pryce, R., 1977. A new class of phytoalexins from grapevines. Cell. Mol. Life Sci. 33, 151-152.
    Li, W., Li, B. G., Chen, Y. Z., 1998. Oligostilbentes [sic] from Vitis davidii. Chinese Chem. Lett. 9, 735-736.
    Li, W., Li, B., Chen, Y., 1998. Flexuosol A, a new tetrastilbene from Vitis flexuosa. J. Nat. Prod. 61, 646-647.
    Li, W., Li, B., Chen, Y., 1998. Oligostilbenes from Vitis betulifolia. Phytochemistry 49, 1393-1394.
    Li, W., Li, B., Chen, Y., 1998. Oligostilbenes from Vitis wilsonae. Chin. J. Appl. Environ. Biol. 4, 28-31.
    Mattivi, F., Reniero, F., 1992. Oligostilbenes from the roots of genus Vitis. Bull. Liaison Groupe Polyphenols 16, 116-119.
    Oshima, Y., Namao, K., Kamijou, A., Matsuoka, S., Nakano, M., Terao, K., Ohizumi, Y., 1995. Powerful hepatoprotective and hepatotoxic plant oligostilbenes, isolated from the Oriental medicinal plant Vitis coignetiae (Vitaceae). Experientia 51, 63-66.
    Ourtoule, J., Bourhis, M., Vercauteren, J., Théodore, N., 1996. First Symmetrical Bicyclo[6.6.0]tetradecane Resveratrol Tetramer from Stalks of Vitis vinifera (Vitaceae). Tetrahedron Lett. 37, 4697-4700.
    Pezet, R., Perret, C., Jean-Denis, J.B., Tabacchi, R., Gindro, K., Viret, O., (2003). δ-viniferin, a resveratrol dehydrodimer: One of the major stilbenes synthesized by stressed grapevine leaves. Journal of Agricultural and Food Chemistry 51(18), 5488-5492.
    Vitrac, X., Bornet, A., Vanderlinde, R., Valls, J., Richard, T., Delaunay, J.-C., Mérillon, J.-M., Teissédre, P.-L., 2005. Determination of stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian wines. Journal of Agricultural and Food Chemistry 53, 5664-5669.
    Wang, K.-T., Chen, L.-G., Tseng, S.-H., Huang, J.-S., Hsieh, M.-S., Wang, C.-C., 2011. Anti-Inflammatory Effects of Resveratrol and Oligostilbenes from Vitis thunbergii var. taiwaniana against Lipopolysaccharide-Induced Arthritis. Journal of Agricultural and Food Chemistry 59, 3649-3656.
    Yan, K., Terashima, K., Takaya, Y., Niwa, M., 2001. A novel oligostilbene named (+)-viniferol A from the stem of Vitis vinifera 'Kyohou'. Tetrahedron 57, 2711-2715.
    Zga, N., Papastamoulis, Y., Toribio, A., Richard, T., Delaunay, J. C., Jeandet, P., Renault, J. H., Monti, J. P., Mérillon, J. M., Waffo-Téguo, P., 2009. Preparative purification of antiamyloidogenic stilbenoids from Vitis vinifera (Chardonnay) stems by centrifugal partition chromatography. J. Chromatogr. B 877, 1000-1004.

Molecular representation

RMN Spectrum


Mass Spectrum

Associations info Plants and parts